When the Plan Meets Reality: Why Adaptability Matters When It Comes To Safety, Security, & Privacy in the Online World

Thirty years of policing taught Darren a lesson that has stayed with him long after retiring from law enforcement, “most plans don’t survive first contact with reality exactly as they were intended.” Police officers spend significant amounts of time training, studying law and policy, rehearsing scenarios, learning tactics, and preparing for situations they hope they will never encounter. All of this preparation matters, but the moment an officer arrives at a dynamic call, the situation can change quickly. New information becomes available, people behave unpredictably, assumptions prove incorrect, and circumstances emerge that were never contemplated during training. At that point, knowing the plan is important, but knowing when and how to adapt the plan can become even more important.

As Clint Eastwood stated in the movie “Heart Break Ridge”, this is where the ability to “adapt, overcome, and improvise” becomes an important skill set. During Darren’s policing career, he occasionally observed officers, supervisors, and even senior police leaders who struggled when circumstances didn’t fit neatly within an established script. They weren’t necessarily poorly trained or inexperienced, in some cases, they knew policy and procedure extremely well. The challenge was that they had become so locked into rote thinking that when something unexpected happened, they struggled to adjust. Rather than assessing what was actually taking place and modifying their response, they continued trying to make the situation fit the plan. In rapidly evolving circumstances, that kind of rigidity can make even a knowledgeable and experienced person less effective.

However, there is an important distinction between adapting a plan and abandoning one. Adaptability doesn’t mean ignoring training, evidence, policy, experience, or established best practices whenever they become inconvenient. Those things provide the foundation upon which good decisions should be made. Adaptability means recognizing that circumstances sometimes change, new information sometimes becomes available, and the original approach may no longer be appropriate for what is actually happening. Sometimes good decision making requires us to stop focusing on the hand we hoped we would be dealt and instead figure out how best to play the hand sitting in front of us.

So, why are we sharing a lesson learned from three decades of policing in an article about youth, teens, parents, caregivers, educators, and technology? Because this philosophy has become an important part of how we approach digital literacy, internet safety, online harm reduction, and artificial intelligence education here at The White Hatter. The technological environment young people are growing up in is constantly changing, and we believe our approach to education and prevention needs to be capable of changing with it. What worked just a couple of years ago may still have value today, but it may no longer be enough on its own.

Our foundation has always been evidence based research. We spend a significant amount of time reading academic studies, examining available data, following researchers in this field who we both agree and disagree with, testing technology ourselves, speaking with youth and teens, listening to parents and educators, and paying attention to how young people are actually using technology. Research matters because it helps separate what we know from what we think we know. It can challenge popular narratives, expose assumptions, identify unintended consequences, and prevent fear, headlines, anecdotes, or political messaging from becoming substitutes for evidence.

However, there is an unavoidable challenge when applying traditional research to technology, technology can evolve significantly faster than the research studying it. Good research takes time. Longitudinal studies can take years, peer review takes time, replication takes even longer, and by the time researchers have developed a clearer picture of one technological behaviour, the platform, feature, device, or the way young people are using it may already have changed. This doesn’t make research less important, it simply means that parents, caregivers, educators, and those of us working in this field sometimes have to make decisions while the evidence is still developing.

Artificial intelligence is a good example. Generative AI, companion style chatbots, AI image generators, nudification technology, synthetic media, smart glasses, voice cloning, deepfakes, and other emerging technologies are developing at a pace that would have been difficult to imagine only a few years ago. Researchers are beginning to examine many of the psychological, social, educational, privacy, and safety implications associated with these technologies, but there are still many questions for which we simply don’t yet have strong longitudinal evidence. Waiting several years for definitive research may be academically appropriate, but it isn’t always practical for a parent, caregiver, teacher, or school administrator who has to make a decision today.

A parent who discovers that their teenager has developed an intense emotional relationship with an AI companion doesn’t have the luxury of waiting five years for longitudinal research to tell them exactly what to do. A school discovering that inexpensive smart glasses can allow a student to discreetly photograph a test, record another student, or capture a private conversation needs to make decisions now. A family dealing with AI generated sexualized imagery, sextortion, cyberbullying, impersonation, or online exploitation needs practical assistance now. These are circumstances where simply saying, “the research isn’t settled yet,” may be scientifically accurate, but it doesn’t provide much help to the person standing in front of an immediate problem.

This is why, when strong evidence exists, we use it as our starting point. When good evidence doesn’t yet exist, is incomplete, conflicting, or hasn’t caught up with a new technological development, we shift toward a risk assessment based adapt, overcome, and improvise decision making process. This means examining what is actually happening rather than immediately assuming either that a new technology is dangerous or that concerns about it are exaggerated. We consider the likelihood of harm, the potential severity of that harm, who may be particularly vulnerable, what benefits the technology may provide, what safeguards already exist, where those safeguards may fail, and what practical steps can reasonably reduce risk while preserving legitimate benefits.

This approach also explains why we are often cautious about one size fits all solutions to complicated technological challenges. It can be appealing to believe that if we simply ban a platform, prohibit a device, establish another age restriction, install stronger parental controls, or pass new legislation, the underlying problem will disappear. Sometimes restrictions are appropriate, sometimes regulation is absolutely necessary, and sometimes access should be limited because the risk outweighs the benefit. However, we also need to ask what happens after the restriction is introduced, whether young people will move elsewhere, whether the policy can realistically be enforced, whether unintended consequences might emerge, and whether the proposed solution actually addresses the behaviour or simply the technology currently associated with it.

We have dipped our toe into legislative advocacy when we believe it is appropriate, particularly around corporate accountability, privacy, safety by design, transparency, and the responsibilities technology companies have toward young people. Legislation can establish important guardrails, and companies should absolutely be held accountable when their design decisions unnecessarily expose users to foreseeable risks. However, legislation moves slowly, technology moves quickly, and youth behaviour can change almost overnight. A law being debated today may take years to implement, while parents and educators are already dealing with the issue the proposed legislation is intended to address.

This is why the majority of our work remains focused on helping youth, teens, parents, caregivers, and educators triage the here and now. We are interested in what young people are actually doing with technology, not simply what adults believe they should be doing, what a company’s terms of service say they are allowed to do, or what we hope future legislation might prevent them from doing. There can be a significant gap between policy and practice, and understanding that gap is critical to meaningful digital literacy and internet safety education.

Over the years, one thing youth and teens have repeatedly taught us is that they don’t always use technology in the way adults believe they do. A platform created for one purpose can quickly be used for another. A feature designed to increase privacy can also be used to hide harmful behaviour. A technology that presents a legitimate risk in one circumstance can provide accessibility, creativity, connection, education, or independence in another. When one platform becomes restricted, young people may migrate to another. When one technological safeguard appears, some will find a workaround. This doesn’t mean safeguards are pointless, it means safeguards should be part of a broader strategy rather than mistaken for the entire strategy.

The same principle applies inside the home. Parental controls can be helpful, but they can’t anticipate every circumstance a young person will encounter. Household technology agreements can establish important expectations, but eventually something will happen that wasn’t contemplated when the agreement was written. A parent can teach a child never to communicate with strangers online, only to discover that the person causing harm is someone their child knows from school. A family can carefully manage social media access while overlooking risks occurring through gaming, messaging, artificial intelligence, or another emerging technology. The digital environment is simply too complex and dynamic for any checklist, filter, parental control, policy, or piece of legislation to anticipate everything.

This is also why we believe digital literacy and internet safety education needs to move beyond simply teaching young people lists of things they should and shouldn’t do online. Rules have their place, particularly with younger children, but as youth grow older, we need to help them develop the capacity to make decisions when there isn’t a rule covering the situation and an adult isn’t standing beside them. They need to understand how to assess risk, recognize manipulation, protect personal information, question what they see and hear, understand persuasive design, recognize when artificial intelligence may be influencing them, identify when something feels wrong, know where to seek help, and recover when they make a mistake, something we call the “human element” when it comes to today’s onlife world.

Perhaps most importantly, we need to teach young people that changing course when new information becomes available isn’t failure, it’s critical thinking. The same should be true for adults. If new evidence shows that something we previously believed about technology was incorrect, we should be willing to change our position. If a technological development creates a risk that wasn’t previously anticipated, we should adjust our response. If something we initially viewed primarily as a risk begins providing meaningful educational, accessibility, or social benefits, we should be capable of acknowledging those benefits without pretending the risks disappeared. Evidence based education should never require us to defend yesterday’s position simply because it was yesterday’s position.

For us, this is the difference between having principles and being locked into a script. Our principles remain fairly consistent, follow the evidence, protect young people from foreseeable harm, preserve opportunities and benefits where reasonable, hold companies accountable for their design choices, help families understand the technology their children are using, and give youth the knowledge and skills they need to navigate their increasingly connected world. What may change is how those principles are applied as technology, research, and youth behaviour evolve.

We can’t predict every technological challenge today’s children will encounter before they reach adulthood. In fact, some of the technologies that will eventually create the greatest opportunities and challenges for today’s young people probably haven’t even been invented yet. Trying to prepare children for every individual app, platform, device, or AI system is therefore an impossible task. What we can do is provide them with transferable skills that remain useful when the technology changes: critical thinking, media literacy, digital literacy, AI literacy, privacy awareness, risk assessment, emotional intelligence, resilience, and knowing when and how to ask a trusted adult for help.

Thirty years of policing taught Darren that preparation matters, training matters, evidence matters, and having a plan matters. It also taught him that sometimes reality doesn’t care about the plan. When that happens, the people who are often best positioned to respond effectively are those who understand their foundations well enough to adapt them intelligently to the circumstances in front of them.

We believe exactly the same thing applies to parenting and educating young people in today’s onlife world. Prepare for what we can,  educate based upon what we know, be honest about what we don’t yet know, assess risk when the evidence hasn’t caught up, change course when circumstances or evidence change, and most importantly, teach our kids how to do the same.

The goal isn’t to create a perfect plan for every technological challenge our kids will encounter. The goal is to give them the knowledge, skills, relationships, and adaptability they will need when the plan meets reality.

Digital Food For Thought

The White Hatter

Facts Not Fear, Facts Not Emotions, Enlighten Not Frighten, Know Tech Not No Tech